Difficult Conversations: 9 Common Mistakes

When difficult conversations turn toxic, it’s often because we’ve made a key mistake: we’ve fallen into a combat mentality. This allows the conversation to become a zero-sum game, with a winner and a loser. But the reality is, when we let conversations take on this tenor – especially at the office – everyone looks bad, and everyone loses. The real enemy is not your conversational counterpart, but the combat mentality itself. And you can defeat it, with strategy and skill.

Mistake #2: We try to oversimplify the problem.

If the subject of your argument were straightforward, chances are you wouldn’t be arguing about it. Because it’s daunting to try and tackle several issues at once, we may try to roll these problems up into a less-complex Über-Problem. But the existence of such a beast is often an illusion. To avoid oversimplifying, remind yourself that if the issue weren’t complicated, it probably wouldn’t be so hard to talk about.

Mistake #3: We don’t bring enough respect to the conversation.

The key to avoiding oversimplification is respecting the problem you’re trying to resolve. To avoid the combat mentality, you need to go further – you need to respect the person you’re talking to, and you need to respect yourself. Making sure that you respond in a way you can later be proud of will prevent you from being thrown off course if your counterpart is being openly hostile.

Mistake #4: We lash out – or shut down.

Fear, anger, embarrassment, defensiveness – any number of unpleasant feelings can course through us during a conversation we’d rather not have. Some of us react by confronting our counterpart more aggressively; others, by rushing to smooth things over. We might even see-saw between both counterproductive poles. Instead, move to the middle: state what you really want. The tough emotions won’t evaporate. but with practice, you will learn to focus on the outcome you want in spite of them.

Mistake #5: We react to thwarting ploys.

Lying, threatening, stonewalling, crying, sarcasm, shouting, silence, accusing, taking offense: tough talks can present an arsenal of thwarting ploys. (Just because you’re trying to move beyond the combat mentality doesn’t mean your counterpart is.) But you also have an array of potential responses, ranging from passive to aggressive. Again, the most effective is to move to the middle: disarm the ploy by addressing it. For instance, if your counterpart has stopped responding to you, you can simply say, “I don’t know how to interpret your silence.”

Mistake #6: We get “hooked.”

Everyone has a weak spot. And when someone finds ours – whether inadvertently, with a stray arrow, or because he is hoping to hurt us – it becomes even harder to stay out of the combat mentality. Maybe yours is tied to your job – you feel like your department doesn’t get the respect it deserves. Or maybe it’s more personal. But whatever it is, take the time to learn what hooks you. Just knowing where you’re vulnerable will help you stay in control when someone pokes you there.

Mistake #7: We rehearse.

If we’re sure a conversation is going to be tough, it’s instinctive to rehearse what we’ll say. But a difficult conversation is not a performance, with an actor and an audience. Once you’ve started the discussion, your counterpart could react in any number of ways – and having a “script” in mind will hamper your ability to listen effectively and react accordingly. Instead, prepare by asking yourself: 1. What is the problem? 2. What would my counterpart say the problem is? 3. What’s my preferred outcome? 4. What’s my preferred working relationship with my counterpart? You can also ask the other person to do the same in advance of your meeting.

Mistake #8: We make assumptions about our counterpart’s intentions.

Optimists tend to assume that every disagreement is just a misunderstanding between two well-intentioned people; pessimists may feel that differences of opinion are actually ill-intentioned attacks. In the fog of a hard talk, we tend to forget that we don’t have access to anyone’s intentions but our own. Remember that you and your counterpart are both dealing with this ambiguity. If you get stuck, a handy phrase to remember is, “I’m realizing as we talk that I don’t fully understand how you see this problem.” Admitting what you don’t know can be a powerful way to get a conversation back on track.

Mistake #9: We lose sight of the goal.

The key in any tough talk is to always keep sight of the goal. Help prevent this by going into conversations with a clear, realistic preferred outcome; the knowledge of how you want your working relationship with your counterpart to be; and having done some careful thinking about any obstacles that could interfere with either. (Remember, “winning” is not a realistic outcome, since your counterpart is unlikely to accept an outcome of “losing.”) If you’ve done the exercise described in Slide 7, this should be easier. And you’ll be less likely to get thrown off course by either thwarting ploys or your own emotions.

In conclusion…

When we’re caught off-guard, we’re more likely to fall back into old, ineffective habits like the combat mentality. If you’re not the one initiating the tough conversation, or if a problem erupts out of nowhere, stick to these basics: keep your content clear, keep your tone neutral, and keep your phrasing temperate. When disagreements flare, you’ll be more likely to navigate to a productive outcome – and emerge with your reputation intact.

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